


Pretty Baby

by bryzknowstheuniverse



Category: IT (2017), IT - Stephen King
Genre: Anal Sex, Blow Jobs, College AU, Crossdressing, Facials, Lingerie, M/M, Mild S&M, Rimming, Sugar Daddy Bill, They are aged up to adult hood, Thot Stan, not the child actors obviously
Language: English
Status: Completed
Published: 2017-11-24
Updated: 2017-11-24
Packaged: 2019-02-06 08:43:16
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,530
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12813864
Author URL: https://archiveofourown.org/users/bryzknowstheuniverse/pseuds/bryzknowstheuniverse





	Pretty Baby

Stanley Uris could not believe that he was fucking doing this right now. This couldn’t be his fucking life.  


  
Two weeks ago on the brink of a mind shattering climax brought on by his boyfriend’s super skilled fingers, Bill had leaned in and huskily whispered in his ear that his dirty fantasy was seeing Stan bent over, ass up, wearing a pretty skirt, makeup, lingerie, and tights, just to get absolutely ruined when Bill’s own cum stripped them. The desperation dripping from Bill’s voice, coupled with the idea that Stan himself could inspire such passion in his boy, made him cum so hard on the spot that he nearly blacked out.   
  
He had passed it off at first, just something Bill had said in the spur of the moment, until he went to borrow his boyfriend’s laptop and opened it to find the browser full of tabs from some Trashy.com and Victoria’s Secret. Stan was taken aback, it stung, he looked at the pictures of models, perfectly molded breasts and curved hips. Stan thought about his own body; flat chested, straight boyish hips, pale, and scrawny. Hair still comprised of corkscrew curls. Of all of his friends, Stan had been the one whose body had decided not to develop. He was only an inch or two taller than Eddie for crying out loud. He was still frozen in contemplation in front of the computer screen when Bill opened the door to the dorm room. Bill went into full panic mode when he saw what Stan had open on his laptop, swearing up and down that he had cleared his browser history. He moved forward cautiously to the curly haired man.   
  
“B-ba-baby.” He uttered carefully reaching to place a hand on Stan’s shoulder. When he got no reaction, he moved to talk again, “S-Stan it’s n-n-not what it l-looks l-like.” He stuttered out, nerves high.   
  
“Is this what you want?” Stan snapped out of his frozen state, “Is this what you want now, Bill? You don’t want me anymore? You don’t find me attractive...I mean why would you when...I’m nothing compared to them...” Stan’s voice broke, tears were filling his vision, he’d loved Bill, only wanted Bill for as long as he could remember. No other human could ever compare for him, but obviously Bill didn’t feel the same way.   
  
“Stan.” Bill said, hints of pain and embarrassment in his voice, Stan took it as pity. Prepared himself for whatever blow was about to come next, Bill was going to leave him for sure. “I...I...I don’t want t-them. I w-was l-looking at w-what they w-were wearing f-for you.” He pushed out, stumbling over his words. He was waiting for Stan to strike out at him, to yell, this was a weird request in all honesty. Bill knew it wasn’t normal.   
  
“What are you talking about?” Stan asked confused. His boyfriend’s words making no sense at all. Why would Bill be looking at half naked pictures for him?   
  
“Uhm...w-well...I kind of like to picture you wearing pretty lingerie and stuff.” Bill rushed out quickly, before his stutter had a chance to interject.   
  
“What?” Stand blanched, “Does this have anything to do with what you mentioned in bed the other night?” Bill nodded, ducking his head in embarrassment. Stan tried to comprehend this and let out a bit of a sigh of relief, “That’s what this is, baby? Your kinky self wants me to dress up all pretty for you? Want to run your hands up my stocking thighs under my skirt?” The other boy choked on his breath and let out an involuntary groan. Hearing his love describe his fantasy was almost too much for him. Stan took his boyfriend’s moan as the response he needed. “Well hell, Bill. Then that’s all you had to say. I thought you were going to leave me for some bimbo with big tits.”   
  
“N-no. Of course n-not. I l-love you, Stanley. Only y-you.” Bill said sincerely leaning forward and pressing his lips to Stan’s in a reassuring kiss, hoping to convey all of his feelings. Stan pulled away before Bill could really have his way with him, and pulled a groan from him.   
  
“Well Billy, let’s take a look at what you like Baby and pick something for me to rock your world in.” Bill almost cried out at the words.   


  
  
True to the shipping description on the website, “Guaranteed Delivery in 5-7 Business Days”, Stan found the box waiting for him in the dorm office when he came back from his Economics class.   
  
He thanked his lucky stars that his longtime friends and dorm mates Richie, Eddie, Mike, and Ben had decided to go to some crap music festival and blown off their Friday classes. Stan was all for making his boy happy, but he wasn’t sure that he would be able to mentally calm down enough and get in the mental space to do this if there was even a possibility of one of them walking in.   
  
He sat staring at the box that sat on the table in the common room of their dorm suite, somewhat afraid to open it. He knew that Bill would be back from class in two hours, and he needed to bite the bullet and get ready. He moved to the wall and picked up the phone, resting the receiver between his shoulder and ear, quickly dialing a number and praying that they would pick up.   
  
“Hello?” Came the response and Stan could have kissed her in his excitement.   
  
“Bev! Oh thank goodness!” He nearly screamed into the mouthpiece and he could imagine Bev wincing holding the phone away from her.   
  
“Hey Stan the Man,” she responded using his old nickname, she always was good for a dose of nostalgia, “what’s up? I thought all of you were going to that blazefest that Richie found out about.”   
  
“Eww no. Anything that Richie thinks is a good time, I’ll pass on.” Stan responded, before chiding himself to get back on track, “Bev, I called because I need your help...”   
  
“What could you possibly need my help with?” She replied surprised, it wasn’t everyday that Stanley Uris asked for helped, it would be more common to see a dog walking on its hind legs.   
  
“I...I...you have to promise not to tell the others. Bill would kill me...” this had piqued Bev’s interest, she and Bill had shared a few brief months of puppy love, most of which was what could be considered long distance when she moved to Portland with her aunt. They had wound up moving back the following summer, her aunt claiming that relocating would be easier than having to listen to Bev cry over missing her friends, her Losers. The Losers Club bond was tight as ever, but her feelings for Bill were strictly platonic, plus she was really waiting for his dumbass to realize that he had feelings for his best friend, none other than Stan Uris. That took until winter break of their sophomore year when Stan finally just grabbed the taller boy by his collar and pulled him down into a kiss, tired of waiting for him to get his head out of his ass and make a move.   
  
“I’ll be over in 15.” she said, no explanation needed. No one blindly supported the two of them more than Bev.   
  
Stan hung up the phone and tapped his fingers on the table, still looking at the offending box. Bev lived in the female dorm on the other side of campus, try as they did the campus housing department would not allow her to room with them. No co-ed rooming was allowed on campus. It was a small price to pay for being able to keep the club together in one place though.   


  
  
“Fucking Hell, Marsh. Stop laughing.” Bev was rolling, literally rolling with laughter across the floor. Stan had only just finished his explanation of why he needed help when she collapsed. Stan tapped the toe of his sneaker against the floor a few times, arms crossed and cheeks flushing with embarrassment.   
  
“Alright, I’m sorry,” Bev laughed, pulling herself together, “I’m so sorry, Stan. Let’s get you ready. You’re so sweet for taking your boyfriend’s desires into consideration and stepping outside of your comfort zone.” Her face was still red and slight tear streaks from her mascara were visible, but she was completely sincere as she moved to find scissors to open the box.   
  
Stan sat silently and waited for more snarky responses as she pulled items out of the box, but Beverly only gasped at how gorgeous the items in the box were. She pulled out a baby blue satin bra, the top of the cups trimmed with matching blue lace. Next out of the box came the matching panties, garter belt, and white thigh high stockings with pure white lace at the top.  Bev turned to look at Stan gawking.   
  
“This is all gorgeous. You are going to look amazing, Bill is going to lose his shit!” She exclaimed. Laying all of the items out on the table, tapping her cheek with her fingertips as thoughts began to swirl in her mind.   
  
“You really think that it will look nice? Even on me?” Stan wondered out loud. Bev gave him a look of disbelief, but kept the obligatory eye roll to herself.   
  
“Oh Stanny Boy, you don’t give yourself anywhere near enough credit. You need to be confident and own it. You hold all the power here.” Stan didn’t look convinced, but she moved on, “Soooo, do we have anything else to work with? Shoes? Make up? Hair accessories? What about the skirt?” Stan blushed, surprised that anything was still embarrassing him at this point, but disappeared into his room and returned with a bag from Target. 

  
  
Stan had gasped as he took in his new appearance in the mirror. It hadn’t taken Bev very long to get him all together.   
  
He stood a bit wobbly on three inch silver satin Mary Jane pumps, the delicate ankle strap the only thing keeping him at all stable. His legs were sheathed in the white nylons, lace bands stretching around his thighs where they attached to his garter belt. He had added a simple yet flirty mini skirt, it was a pale mint. Bill had mentioned once that he liked the color, Stan just never thought that he would use that knowledge for this exact purpose. He had stolen one of Bill’s white button down shirts and left the buttons undone, Bev had carefully tied it so it would show off a bit of his waist and his pretty blue bra. She had worked wonders with the bit of makeup that he had bought as well. His skin looked flawless and seemed to glow, just the right amount of rosey accent on his cheeks. She had somehow made his eyes look way bigger and brighter with shimmery eyeshadow, mascara, and black eyeliner flicked out into a perfect cat eye. Stan’s lips were a glossy pale pink with a hint of shimmer. His hair was the finishing touch, Bev had twisted a few tendrils backs and away from his face using a touch of gel and secured them with sparkly barrettes, she fluffed the rest of his hair out to add a bit more volume.   
  
He couldn’t believe it. He looked...pretty. He looked stunning if he did say so himself, he wished he could look like this all the time. He finally understood the allure that Bill saw in Stan dressing like this, because he did too.   
  
He hugged Bev goodbye and thanked her a million times, promising to give her details the following day, and leaned against the armrest of the couch. Bill would be home any minute.   
Stanley Uris could not believe that he was fucking doing this right now. This couldn’t be his fucking life.

 

Bill was pissed. Like next level pissed. His stupid Medieval Lit professor didn’t do jack shit, and certainly didn’t actually read Bill’s carefully researched and well thought out paper before slapping an ugly ass “C” on it. Bill Denbrough didn’t get “C”s, hell he freaked out if he got too many “B”s. He worked hard because he loved the content and knew that he needed a high GPA if he had any hope of actually getting a job with a damn English degree.

He half considered heading over to the health center and taking his frustration out on a punching bag, but he would rather just have Stan wrap his arms around him and tell him that everything was going to be alright. With Stan his anger always managed to dissipate, no one could take care of him the way his boy did.

Bill took the stairs to the fifth floor to help rid himself of some frustration, he was of course one of those freaks who thoroughly enjoyed exercising and used it to relieve tension, Mike was the only other Loser who agreed that this was acceptable, everyone else thought they were both bat shit crazy. Bill reached the fifth floor and headed down the corridor to where their dorm suite was located. They were on the very end, Bill frequently wondered if they just knew that the boys were going to be loud when they submitted their application for housing, and stuck them in the last suite on the top floor, blocked off by cinder block to try to keep them from disturbing other residents.

He reached into his pocket and pulled out his key, slotting it into the hole and gently pushing the door open when it unlocked. He closed the door and swung his backpack off his shoulders before he finally looked up.

Stan was sitting on the arm of the couch, legs spread slightly and chest pushed out, glossed lips pouting. Bill’s eyes shoot from the heels, to the baby blue bra, to the skirt, and holy shit Stan was wearing Bill’s shirt. Jesus, Bill had never seen anything so Goddamned beautiful and sexy in his whole life.

“Mmm baby, I thought you were never going to come home, I thought I was going to have to take care of myself and start on my own.” Stan moaned out with a smirk.

Bill nearly came in his pants right then and there.

 

 

Stan could feel his confidence blooming even further, his boyfriend looked like he was in pain from the amount of pleasure he was in, and Stan hadn’t even touched him yet. He strutted up to the other boy, smirk never leaving his mouth. Bill was shaking with anticipation, Stan reached up to whisper in Bill’s ear, thankful that the heels did some of the work for him because his boyfriend was well over six feet and Stan was lucky to be considered five foot seven most days.

“I’m going to make you feel so good, you want that right, Billy? Want me to make you lose your damn mind with pleasure?” Stan whispered seductively, he had no idea that this side of him existed, but he liked it. Bill whined out in response, unable to form words. Stan pressed a chaste kiss to his cheek and stepped back, turning to head to their bedroom, making sure to sway his hips as he went. He mentally fist bumped when he heard Bill behind him racing to keep up.

Bill closed the door behind him, and then was immediately slammed back against it by Stan. He didn’t even have time to steel his nerves before Stan was sinking to his knees in front of him, he made quick work of unfastening Bill’s belt and jeans, pulling them down his legs so Bill could kick out of them and toe off his sneakers. His boyfriend played with the waistband of his boxers, but made no move to actually take them off, just ran his hand up Bill’s stomach over his subtly defined abs. Bill moved to strip off his shirt, tossing it onto the growing pile of his clothing. Stan bounced back up onto his feet and stepped back taking a look at his boy.

Bill stood absurdly wearing just his boxers and his striped tube socks, a blush spreading from his cheeks down his chest. He was so damn hot, but Stan wasn’t giving in that easily. He was going to make Bill work for it.

“Bed. Now.” Bill scrambled to comply, he sat on the end of the bed waiting for Stan’s next order.

“G-g-god St-stan, you l-look so f-fucking perfect, b-baby. So fuc-fucking pretty.” Bill stumbled out, he couldn’t take it anymore, his pretty baby was driving him nuts.

“Only for you, babe. Only for your eyes.” Stan said while moving to sit in Bill’s lap, he ground down lightly and felt that Bill was already rock hard and ready to go. Bill grabbed Stan’s hips to still him, he was going to come embarrassingly fast if the smaller boy kept it up. “Tell me what you want, you can have whatever you want, but you’re going to have to say it.” Stan teased. 

“S-sh-shit. W-want you t-to suck m-me off.” Bill groaned, “W-want those p-pretty glossed lips around m-my c-cock.” Stan hummed, letting Bill know to continue, “T-then I want to r-rip those p-pretty panties off of y-you, and eat y-you out u-until you are c-crying with antici-pation, and then I’m g-going to p-p-pound that t-tight ass of y-y-ours until y-ou screm a-and c-cum and then I’m going t-to pull out and c-cum all over th-that pretty f-face.” Stan groaned, he wanted all of that so bad. So so bad.

He pushed Bill back so he was lying down, and nudged him to move further up the bed. Stan knelt between Bill’s legs, hooking his fingers into the waistband of his boxers and pulling them down. Bill hissed as his cock sprung free from its confines and the cool air hit it. He was painfully hard now, Stan could see that. He knelt forward and allowed his breath to ghost over the head, Bill’s dick twitched and pre cum leaked from his slit. Stan couldn’t stop himself from looking Bill dead in the eye and licking his lips. 

He loved the teasing, but he leaned down and licked a stripe up the side of his cock, Bill’s moans becoming his soundtrack, cheering him on to continue. He slipped the head in his mouth and sucked, Bill cried out in pleasure, and Stan without skipping a beat began to take him all the way down. He swallowed around his dick, willing his gag reflex to stay away. When he needed to take a breath he began sliding his mouth up and down, alternating between nose resting in Bill’s well kept happy trail and tongue swirling around the tip.

Bill could feel his stomach tightening. He knew what would happen next, if Stan didn’t stop. He pushed on Stan’s shoulder, urging the boy to pull off, but Stand just looked him dead in the eye and kept up with his torturous suction. “B-baby p-please, I’m g-gonna cum.” He warned again, plea falling on deaf ears. Bill couldn’t hold on anymore he shouted out and he realeased his loud down his boyfriend’s throat. Stan kitten licked his head, making sure he got every single drop from Bill.

Bill sat up and pulled Stan into a filthy kiss, tasting himself on Stan’s tongue. They made out lazily for a few minutes, Bill softly palming Stan under his skirt through his silky panties. He could feel a wet spot forming on the fabric, Stan getting more and more desperate. He reached around, rubbing his hand over Stan’s plump ass and then lifting his hand to slap it. Stan let out a surprised squeak, but arched his back out more so Bill could do it again.

“H-hands and kn-knees now, L-little S-slut.” Bill said, taking control. Stan was running the show, but hot damn did he love it when Bill got impatient and took control, so he scrambled onto his hands and knees, presenting his ass to his boy for the taking. “G-good boy.” Bill praised, running his hands up and down his ass, he pulled down the blue satin, revealing Stan’s milky mounds. Bill could see a small reddening where his hand had made contact with with the smaller man’s ass. He couldn’t help himself, he rested his hand against the mark before lifting it and adding to the redness, he did this until he could see the definitive print of his hand mark his boy’s ass and Stan was writhing in pleasure underneath him. “Y-you like that, d-don’t you s-slut?”

“Y-y-es! Holy shit, yes!” Stan screamed, he wanted Bill in him, wanted Bill to get on with it now. “Fuck my ass with your tongue, baby. Open me up for that big cock of yours, I want you to pound be into the fucking mattress.” Bill smirked at his boyfriend’s desperation, enjoying the momentary role reversal.

Bill got to work, he pressed light kisses down Stan’s spine, watching as the other boy falls apart more. He spread his cheeks and looked at Stan’s perfect puckered pink hole. Watched it twitch as an invitation, just waiting for Bill to devour it. He licked a stripe over it, keeping his tongue flat as he repeated the motion. Stan was crying out, lost in pleasure. Bill took the opportunity and works the tip of his tongue into his hole, stretching the opening slightly until he could full on fuck into his boyfriend’s sweet asshole with his tongue. He did so with reckless abandon, jaw aching, and Stan falling to his elbows, unable to hold his own weight.

“T-ta-take off the shirt, i w-want to s-see t-that pretty b-bra.” Bill requested before reaching his hand around to Stan’s front, collecting some precum from the weeping head and using it to slowly jerk Stan off teasingly. Stan complied with Bill’s instruction but was clearly waiting for Bill to do even more, but that’s not how Bill plays. He wanted the other boy to beg.

“Please!” Stan cried out, he wanted to cum so bad, but also wanted to feel all of Bill inside of him even more. Wanted to be stretched open on his boyfriend's huge cock, wanted to feel the shocks of Bill pounding into his prostate over and over again like only he could. 

“P-please, what?” Bill asked, playing coy, moving his mouth away from Stan’s hole, but keeping his hand working on his dick. He was already reaching for the bottle of lube, that Stan had left on the side table.

“Please...please...gah...please fuck me, want you inside of me Baby, need to feel you.” Stan babbled and Bill finally gives in to his requests. He removed his hand, and moved to coat his own cock with lube, he quickly coated three of his fingers as well. Stan was already loose from the assault of Bill’s tongue, so it took no time to scissor two fingers into his hot hole and then slip a third in. “I’m ready, Bill I’m fucking ready, get your fingers out of my ass and stick that big and thick penis of yours up my ass...” Stan whined, but was cut off when Bill pushed in to the hilt with no warning. He cried out at how full he felt.

Bill pounded into him, just like he asked for. He looked at his beautiful boyfriend, his blue satin bra contrasting against the pale skin of his back, skirt hiked up around his hips so that Bill could take his ass and use it, and those damn stockings on his legs, Bill was buying him so many more of those.

Stan’s ass was warm and tight, no matter how many times they have done this, Bill was always mesmerized by how his boyfriend feels. If he could only do one thing for the rest of his life, he could honestly say that it would be fucking, Stan. He could feel that Stan was getting close, sharp gasps and moans leaving him. He angled his hips and felt Stan seize as he hit his prostate, and smiled to himself before pounding harder into that spot with every thrust.

He pulled Stan up so he was on his knees, back leaning into Bill’s chest. His hand pulled down one of the cups of Stan’s bra, tweaking his nipple as he continuing his ruthless thrusting. Stan was crying, begging Bill to let him cum. Bill obliged, he wrapped his hand around Stan’s dick and in three strokes, Stan was screaming and Bill could feel Stan’s dick pulsing as warm cum flooded over his fingers. He held his hand out for Stan, and he licked his own cum up, swirling his tongue around Bill’s fingers to get it all. Bill thrusted lightly one more time, before motioning for Stan to turn around. 

Stan did one better, he got off of the bed and sunk to his knees, tilting his head back slightly. Bill began jerking himself mercilessly, pulling himself closer and closer to the edge, aching to paint his boy with his cum. Show him just how much he was his.

“Come on, you can do it.” Stan urged him on, “Cum on my face, Daddy.” Bill fucking lost it when Stan called him that, he came harder than he could ever remember doing before, his huge load landed all over Stan’s face and chest. He sat heaving for a moment, coming back to himself when he heard Stan.

“Shit baby, that really got you, huh? You like being called Daddy, don’t you? That’s so hot.” Stan whispered in his ear, pulling him in for a soft and slow kiss. “But fuck, I don’t know how I’m going to get the stains out of my bra…” He pouted.

“I-i’ll buy you a-another one. A-an-anything you w-want, just s-say the w-word.” Bill stuttered, out of breath. He pulled a few tissues out of the dispenser and began wiping his cum off of Stan. 

“Ooooooh, Sugar Daddy William Denbrough, I could definitely get used to that.” Stan giggled.

Bill pulled Stan up from the floor and towards their bathroom. This was not a clean up job that could be accomplished with just tissues. Bill started the shower, adjusting it to Stan’s preferred temperature, because he was amazing like that. Stan stripped himself out of all of his pretty clothes. Bill had him sit on the counter, carefully unbuckling his shoes and letting them drop to the floor, before rolling the stockings down Stan’s thighs. Stan reached up to remove his sparkly barrettes and leaves them on the counter. Bill helped him step in the shower, and began to lather shampoo into his curls, making sure to get all of the gel out.

Stan felt so loved and cared for. How could he have ever gotten so lucky to find someone like Bill? Someone who worshiped him and made him feel so pretty?

 

Stan couldn’t believe it. This couldn’t be his fucking life.


End file.
